The Dilemma
by iWatch2much
Summary: ***Caution NOT EVERYTHING IS AS IT SEEMS*** R/T R/L I did not know who to put this fic after because it has such a random collection of characters and I have no idea where im going to end... SO come on this journey with me featuring: RORY!
1. Chapter 1

**SO im sorry for neglecting my other story but I was rewatching Gilmore girls and thought of a great story to put up. This is just the beginning so stay tuned. ALSO, follow me on my twitter MaRa2326! **

We weren't friends, no. But we were getting there and that is enough for me. As I walked into the large marble room with the grand piano I mentally checked off "befriend a former enemy" off of my bucket list.

Yes I had a bucket list. I also had multiple pro/con lists, book lists, and to do lists as well, since we are on the subject.

I looked up and met his puppy dog eyes. He was pressing random keys on the piano in his own world. I felt bad for him, but not pity. The kind of bad that fills you up as if you are the victim. The kind that makes you want to hug the person and be there for them. Not the kind that makes you looks at them with judgment in your eyes.

As the evening progressed on we spoke about Summer, biology, spanish, Dean, and then something quite unusual happened.

He kissed me. A good hardy not-too-much-of-anything kiss. And it was sweet and different and completely and totally perfect. Until I pulled away, and everything I had been feeling about Tristan and Dean and….oh God and HIM.

It is safe to say I bolted. I mean bolted faster than a Russian after the last shot of vodka on earth. That is how fast I ran. An apology was mumbled on my part but then I grabbed Lane and ran. Ran straight into HIM.

I didn't need to look up to know who it was. I stood frozen in his arms, his scent filling me up.

The tears on my eyes dried but anger replaced my sorrow.

"Are you happy?" I screamed. I don't get angry easily, especially in front of Chilton people. But this is a very very special occasion. "Go ahead say the words! I don't care because you're just a stupid dumb dodohead poopface."

I grabbed Lane by the wrist and dragged her outside before he could respond. Into the jeep they went and by that time Rory had cooled down.

"Rory? Who was that?" Lane stuttered a little in fear. She had never seen me seethe in that way. Not even when we were little and Lane threw one of my books in the mud.

"What was what? I asked innocently.

"Rory who was that?"

"That was Logan. All blonde haired, blue eyed, smirky, annoying, rich boy bits of him."

"We will get back to the fact that I have no idea who that is and say this….Are you okay?"

"Yeh I'm fine." I turned on the ignition and pulled out of the party. Lane and I sat in awkward silence for a while.

The car pulled up to Lane's house in pure silence. Lane was the first one to speak up.

"Call me tomorrow. We'll talk about this tomorrow. Okay?"

"Okay." I felt ashamed and silly. I drove to Lukes wanting some very fatty food and a large cup of coffee.

"I should have known that life was too cruel to let me have just one good thing. " I got out of the car and walked into Lukes. Luke was scrubbing the counter mindlessly as something was sizzling on the grill. I sat down and sighed.

A cup of steaming hot coffee, black, was placed before her. "I don't condone this. Not even a little. You're rotting from the inside out." With that Luke went into the kitchen and came out with a burger for the boy beside me.

"Don't, please, don't say anything."

"Wasn't even planning on it. Just going to sit here and eat my first ever Lukes burger. Though I have heard great things about it."

"UHHH Finn." He remained silent, as requested. Took a bite out of his burger. She smiled slightly at the irony of the situation. Him saying nothing, really said too much.

Soon he got up slid a napkin under my cup and left placing a quick kiss on my cheek. I heard the door jingle in its familiar way and Finn walk out.

The napkin read:

_Call me baby, anytime, just not in the morning between 4am and 1pm. _

_Kisses, Finn_

I banged my head on the counter. Dropped a 10 dollar bill on counter and walked out, smashing right into yet another person. Tonight just wasn't my night.

Scratch that… this week just wasn't my week.

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	2. Hysterica

**Sorry for the wait, but I kind of needed inspiration! So here is the next chapter, review if you want more.**

Soon he got up slid a napkin under my cup and left placing a quick kiss on my cheek. I heard the door jingle in its familiar way and Finn walk out

The napkin read:

Call me baby, anytime, just not in the morning between 4am and 1pm. 

Kisses, Finn

I banged my head on the counter. Dropped a 10 dollar bill on counter and walked out, smashing right into yet another person. Tonight just wasn't my night.

Scratch that… this week just wasn't my week.

"Dean?"

"Hey Rory, sorry didn't see you there."

"Obviously." I said it a bit rudely, but hey, today just want my day.

"Dean I-" "I should-" We spoke at the same time. He looked down and rubbed the back of his neck nervously. I just stood there biting my lip. Awkward was too mild an adjective for what was happening here.

Suddenly a new wave of confidence hit me. I grabbed my phone and dialed Finn.

"_Hello Darling"_

"_Finn Honey, I think I want to come with you. Can you make your way back and pick me up?" _Dean looked at me like a deer in head lights.

"_Of course I can baby. I will be there right-" _ He hung up the phone as his fabulous black convertible porche up to the curb.

"Well it was nice seeing you Dean but I really must be on my way!" At this point Finn had gotten the car and opened the passenger door for me. He may not be a morning person, and he might drink WAY too much, but all in all he was quite the gentleman.

Dean's mouth continued to hang open as we pulled away. I was soon over taken by a hysterical fit of giggles that I couldn't quite control. Tears started to pour out of my eyes and Finn acted like it was all completely normal. This is why I love having him as a brother.

Well he's Australian and obviously not my brother by blood, so I guess I should explain the situation. Mom and Dad were in Australia getting married a few years back when they stumbled upon a newspaper. In it was an article about a very rich kid newly turned orphan when his house burned down.

Mom being the major softy decided to pay him a visit. This all being very sad and movie like. As soon as they had met Finn and Mom became the best of friends, going shopping together, and inside jokes. So, mom convinced Chris to adopt Finn legally into the family. When they all got back to the states, this got kind of rocky.

Finn was constantly partying and making the wrong friends. That is until mom and dad set him straight, and I helped a bit of course.

Since then Finn and I have been there for each other 100% of the way.

We pulled up at the front gates and left the car for the valet. We have the house in Stars Hollow to get away from society in, but most of the time we live in the mansion in Hartford, its closer to school.

Finn stopped me at the door before we had a chance to go in.

"I love you darling but your brain is not on straight, and that me saying that. SO I think I should warn you. It won't get better unless you sort out this mess you have with Dean, Tristan, and Logan. Not to mention the fact that Jess is head over heels for you."

"I know Finn. I know."

I just got out of the shower the next morning when I checked my phone. A text from Dean and Lane, and 2 missed calls from Logan.

I instantly deleted the text from Dean because frankly, I no longer felt broken when I thought about him. I just want to move on.

Lanes text: **Call me. We need to talk.**

I quickly typed my response: **I cant answer any of your questions until I figure my head out. Can we talk next week. I promise to explain it all then. **

I then got dressed in my Chilton uniform and went to the kitchen.

I grabbed a muffin and the cup of water that was generally left on the counter by mom on her way to work so that I could wake Finn up.

I took the cup into his room but upon nearing the door overheard him on the phone.

"I know Logan I'm worried to but you need to relax, I'm sure she's not ACTUALLY mad at you."

"She's just stressed mate."

"Go grab a fag or something and stop bothering me, your starting to sound like a girl" With that he hung up and I rushed back to the kitchen to eat my muffin. (Author's note: FAG is the slang word for cigarette, not an insult!)

_Logan is worried about whether or not I'm mad at him? Interesting. Why is it that the thought of Logan in the morning is so distracting?_

"Rory? Earth to Lorelai Leigh Gilmore the third?"

"Huh?"

"What were you daydreaming about the Doctor and his magic blue box again?"

"Huh?"

"That was my way of making fun of your television addictions while asking if your mind was on another planet. Come on Rory, you are usually sharper than that."

"Hardy har har. Lets get to school."

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